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Cruising Maine’s Penobscot Bay

• By David H. Lyman
• Updated: June 30, 2021

This summer, with the pandemic and social distancing still in mind, taking the family on a Down East cruise to Maine might be just the thing. After all, it’s not only one of the world’s great sailing destinations, but also there are isolated coves, vacant beaches and uninhabited islands where self-isolation is just fine. If you take your own boat, there are ample shore services, yards, marinas and harbor towns in which to haul or moor your vessel between visits. Or you can charter a bareboat or reserve a crewed yacht. Let me provide an overview of what’s entailed in cruising Maine in the second summer of COVID-19.

The coronavirus restrictions remain fluid, and of course you’ll need to investigate the current situation before shoving off. Now, on to the fun stuff.

Sailing to Maine is the easy part.

It’s only 144 nautical miles on a rhumb-line course from the Cape Cod Canal to Monhegan Island. At 6 knots, that’s 24 hours. It’s another 24 miles up through Muscle Ridge Channel to Owls Head Lighthouse—the front door to what I feel is the greatest cruising ground anywhere: Penobscot Bay.

The distance from York Harbor, near the southern border with New Hampshire, all the way to the Canadian border is 200 nautical miles in a straight line…but the Maine coastline is anything but straight. If you add in the shoreline around each of the 4,500 islands—then include the coves, bays, harbors and tidal rivers—Maine has more coastline than the rest of the entire East Coast, more than 5,000 miles. Logic suggests there must be a few places along that stretch where you can find a secluded spot to anchor for a spell.

Maine’s largest bay, Penobscot, is split down the middle by a chain of islands: the Fox Islands to the south, Islesboro to the north, with a dozen small islands in between. There are half a dozen harbor towns, some small fishing villages, and lots of isolated coves in which to anchor. You’ll find uninhabited islands and beaches to explore, mountain trails to hike, waterfront restaurants and seafood shacks, and open-air farmers markets. There’ll be blueberries to pick, corn to shuck, lobsters to boil, and quiet evenings aboard in your own boat.

Nice, right? Now let’s get to the particulars.

The two-week cruise I’ve outlined below will keep you and your crew safe, in your own bubble, on your own boat. Each day includes a few hours of sailing to a new anchorage. Afternoons are for exploring uninhabited islands, secluded coves and a few villages. Evenings, you are alone, anchored in a secluded cove, as the sun drops behind the Camden Hills. There are enough wilderness islands there to fill up a few weeks—if not the entire summer, and many summers to come.

I’ve lived on and cruised along the coast of Maine for 50 years, and my ideal two-week getaway would be a circumnavigation of the Fox Islands. A couple of kayaks and a RIB with at least a 10 to 15 hp outboard are essential for this kind of serious gunkholing. The anchorages I’ve described are no more than a few hours apart, affording the crew some time to test their sailing skills, and the navigator to plot courses to keep everything off the rocks. You may also find your own anchorages. There are untold options galore, so go explore. I won’t mind at all.

Day One: Rockland is a good place to start (and also a good spot to leave your boat between visits). This large commercial port is easy to enter, with ample space for anchoring. There are rental moorings, docks, fuel, four marinas (including a mega-yacht facility), a large chandlery (Hamilton Marine), supermarkets, canvas shop, mechanics and boatyards. Main Street is abuzz with shops, a theater, two art museums, lots of art galleries, and half a dozen restaurants; the four-star Primo eatery is also nearby. Cape Air provides regular service to Boston from the local airport; the Concord bus line stops at the ferry terminal twice each day. US1 passes through town, and rental and loaner cars are available. Box stores are a few miles out of town. It’s almost civilized there.

To kick things off, leave Rockland midmorning and steer northeast for Pulpit Harbor on the northwest corner of North Haven Island. It’s only 10 nautical miles, and with a southerly breeze, you’ll be there by lunch. Leave Pulpit Rock, with an osprey nest atop, to starboard and find a spot to anchor inside. The moorings are all locally owned, so find a spot in midharbor in 25 feet of water to anchor, or in the two coves on the south side.

There’s a public dock farther in for your dinghy. The island’s food store is a half-mile walk south, from the bridge. Take your dinghy farther up into the cove, past the traffic bridge. Farmland, fields of lupine, and cottages covered in roses line the banks and roads. In the summer, the sun sets over the Camden Hills across the bay well after 8 p.m.

Day Two: Two options: north around the top of North Haven, or south. The wind that day will dictate. The northerly route offers up a scattering of islands with four possible anchorages. Hank and Jan Taft have described these in their comprehensive A Cruising Guide to the Maine Coast (see “Resources and References,” page 51). The Barred Islands and Butter Island are accessible and a good place for lunch, beachcombing, a hike, or even an overnight stop in settled conditions.

Quick aside on dinghies: Finding a place along these islands to beach a dinghy is one thing; securing said dinghy is another. Pull it up on the beach, and when you get back from your hike, you might find that the tide has floated it off the beach and it’s drifting away, or it’s high and dry, 30 feet from the water’s edge.

There are numerous techniques to solve this problem. The captain can drop off the landing party and return to the yacht for a nap. Go ashore in kayaks; they are easily pulled above the high-tide line and carried back. Or rig a dinghy-retrieval mooring system: Secure a floating buoy to the dinghy anchor line with a shackle. Drop it in deep water. Nose into the beach, off-load, then with a long loop of line rove through a shackle on the anchor float, pull the dinghy back out to where you dropped the anchor. Tie the shore end of the loop to something above high tide. When you get back, just pull your dinghy in to the beach. Make your own, or try West Marine’s Anchor Buddy, a ready-made dinghy mooring system using a long bungee cord that snaps your dinghy back out into deep water.

Days Three and Four: With a fair breeze, steer southeast from Butter Island, down to Oak Hill on the tip of North Haven. Give the hodgepodge of small islands and ledges a wide berth on the way. Mind the current. There are two possible anchorages: Marsh Cove, below the hill on which sits the Watson Estate. No access ashore. Mullen Cove is better. The beach provides access to hiking trails through a town-owned park. Just south is Burnt Island, now a North Haven park, with a walking trail all the way around and a float to which you can tie a dinghy at any state of the tide. Or head for the beach off the northwest tip of Calderwood Island. You can’t go wrong with any of these.

Calderwood is tucked in between Simpson and Babbidge islands on the northeast side of the Fox Island Thoroughfare. Uninhabited and open to the public, it is now owned by Maine Coast Heritage Trust, which keeps the trails open now that the sheep have left. There’s a spruce forest at the southern end where the kids can build fairy houses. Anchor off the beach on the north side where hiking trails begin. Be aware of the rock in the middle of the anchorage. I spent a few hours there once waiting to be floated off. This is a popular anchorage, and if too crowded, there’s another spot to the east, between Calderwood and Babbidge. Two beaches provide access ashore and to the trails. The passage between the two islands is strewn with ledges and rock. When departing, go back around the north side of Babbidge or Calderwood. Calderwood might need two days to fully explore. I’ve spent weeks there photographing.

Nearby are two obvious anchorages for the night: Carver Cove, south of Widow Island, is calm, with views of saltwater farms, fields and forests. To the north, past the Goose Rocks spark plug lighthouse is Kent Cove. There’s no shore access, but if there’s a breeze, there’ll be no mosquitos.

Day Five: You have decisions to make: You could go east to Stonington, the Deer Isle Thoroughfare, and on to the islands farther down the Maine coast. (We say “down” up here in Maine when heading up the coast, as in Down East. The prevailing winds are southwest, meaning you’re mostly sailing “downwind.”)

But for the purposes of this itinerary, that cruise is for another time. So we’ll head west through the Fox Islands Thoroughfare, a narrow body of water separating North Haven from Vinalhaven. It’ll be busy with schooners, fishermen, gleaming classic yachts, and powerboats of all sizes passing through. The shore on the south side has a few summer cottages from the previous century. In the 1800s, Maine was a summer retreat for the wealthy from Boston, Manhattan and Philadelphia. With extended families and servants, they arrived by steamship to “camp out” in rambling cedar-shingled cottages. These “cottages” might look small from offshore, but up close, they are massive mansions with dozens of rooms, rambling porches, and servant’s quarters. They are still there. In recent years, the wealthy have returned to buy up fishermen’s shore frontage to erect even-more-lavish estates, with a jet-powered Hinckley picnic boat tied to the dock.

On the north side of the thoroughfare is the small village of North Haven, established by wealthy New York yachtsmen in the last century. North Haven is a world apart from its neighbor, Vinalhaven. The only grocery store is in the middle of the island, but the village might have places to order lunch, ice cream or dinner. This changes annually. Anchor outside the mooring field and out of the ferry’s approach to its terminal. Dinghy docks line both sides of the ferry terminal. The village has a library, art galleries and a community center with frequent performances, plays, lecturers and concerts. The roads wander inland past Victorian cottages, farms, fields and forests. Eric Hopkins, an island painter with a wide reputation, has a studio and gallery in the village, and there may be others. Seasons change, as do the residents.

Spend the night at anchor, or duck around to Perry Creek, a narrow cove on the south side of the thoroughfare. Ashore is a wilderness park with walking trails. Wander through spruce forests, over ledge outcroppings with views. It’s tight in there, but there are a few moorings that can be used by transients for a donation to the Vinalhaven Land Trust. Or drop the hook at the eastern entrance in 20 feet of water. If that’s too crowded, head farther south into Seal Cove. Watch the chart closely because rocks are about, but you should be able to find a spot with sufficient swing room. Take the dinghy back up to Perry Creek, where there’s access to the trails on the southeast side. Watch for a sign nailed high up on a tree. Set your dinghy moor and climb ashore.

Day Six: Heading west down the thoroughfare, pass Browns Light to port, the Sugar Loaves to starboard. You’re heading to Leadbetter Narrow. Pass north of Dogfish Island. To port is Crockette Cove, where there’s room for a boat or two, but mind the underwater cables. At high tide, you can take the dinghy or kayaks a mile and more up into the cove. There are more anchorages on the other side of Leadbetter Narrow.

Narrow is the operative word. It’s a tight squeeze between Leadbetter Island and the mainland of Vinalhaven. Steer north of the green can that marks a rock in the middle of the gap. The current is swift through there. Pass through, and you are at the head of Hurricane Sound, surrounded by a string of islands to the west and Vinalhaven to the east.

There is a lot to explore there, but first get the boat anchored. There’s a nifty spot to the east of Turnip Island, a small tree-topped isle at the entrance to Long Cove, a milelong fjord carved into the solid granite of Vinalhaven Island. There is an abandoned quarry on the hill that provided building blocks for the post offices in Boston and New York in the 1800s. At that time, more people lived and worked the granite quarries on Vinalheaven than live there now.

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The entrance into Long Cove, to the east of Hall Island, narrows to 200 feet, but once through, the cove opens up into a quiet pond with room for a few boats to anchor. The shoreline is tall, covered in spruce. There are a few floating docks along both sides of the shore. Pathways lead up to large private estates. No access there.

A third of the way in, there’s a ledge barring the way, so take the dinghy and explore. Be back before the tides are low because the bar might be too shallow to navigate.

Day Seven: From your anchorage in or near Long Cove, there are small coves and islands—including Fiddlehead and a spot called the Basin—to explore. Use the kayaks, but someone should be in the RIB as a chase boat. The Basin is a large, almost landlocked body of water that’s worth a whole day fussing around in small boats. The narrow entrance to the Basin provides a reversing-falls effect, so enter at slack tide, or with the RIB. Be warned: The narrows can be a whitewater experience.

Day Eight: There are dozens of small islands to the west, a few with limited anchorages. One is south of the neck between Lawry’s Island and Cedar Island. There’s enough room for one, so leave early enough or give it a pass if someone is there. Farther south in Hurricane Sound are White and Garden islands, with two possible anchorages. Go ashore on the beach and take in beautiful vistas of the Camden Hills, and across to Owls Head.

Day Nine: Sail south to the anchorage and mooring field off the east side of Hurricane Island. In the 1800s, this island was a bustling community working the granite stone quarry, still visible today. In the 1970s and ’80s, it was home to the Outward Bound School. In 2009, the Hurricane Island Center for Science and Leadership took over the site, with science, technology, engineering and mathematics experiential education programs for youths between the ages of 11 and 18. Guest rental moorings might be available, and you are invited to go ashore. Anchoring is possible, but the bottom is rocky, with kelp. There are trails around the island and a center to visit.

You’ve been gone a week now, and you might need a few provisions. There’s a small grocery store nearby in Carvers Harbor. You can get there by going southeast around Herons Neck light or up and around Greens Island, then down the Reach, a narrow, twisty passageway between Vinalhaven and Greens Island leading to Carvers Harbor, the main settlement on the island. Keep an eye on the chart and markers as you go because they can be confusing. You might meet the ferry on its way to or from Rockland.

Just before the ferry terminal, drop the hook off Dodge Point or on the opposite side of the entrance, south of Potato Island. Send in the dinghy to see if there is a rental mooring available. Look for a buoy with a bottle wired atop a stick. It’s for the rental fee. Call the harbor master if necessary (207-756-0209).

Carvers Harbor is one of Maine’s busiest lobster-fishing harbors, landing some 5 million pounds of lobster annually. The harbor is narrow, full of lobster boats, and the shore is lined with floating docks piled high with the traps, wood crates and scales. It’s there where fishermen offload and weigh their haul, and cash out. There’s no room in the harbor to anchor, and the bottom is too hard anyway, so anchor outside.

There’s lots to do ashore, so take the crew to the dinghy dock at the head of the harbor, where you can tie up. Across the street is the Nightingale Restaurant, formerly the Harbor Gawker. There are shops, a grocery store, art galleries, pubs, offices and buildings that date back to when this town was a granite shipping port. The streets lead to lanes, past Victorian homes and farms, summer estates, forests, and abandoned, water-filled quarries. Stay overnight because tomorrow will be a long day.

Day 10: It’s just 4 miles from Carvers Harbor to Brimstone Island, a tall, rugged, uninhabited island on the outer edge of Penobscot Bay. It might as well be on the edge of the world. Anchor off the pebble beach at the northwest corner. This is a day-only anchorage. The bottom is rocky with kelp. Holding ground is better on the south side between Brimstone and Little Brimstone but only in settled weather. Dinghy ashore, but keep an eye on the tide or set a dinghy mooring.

The island beach is famous for its small, round, black basaltic pebbles, polished smooth by 100,000 years of wave and tidal action. The stones arrived there eons ago from far, far to the north, carried by the ice sheet as it moved slowly south. I’ve carried three of these small black stones in my left pocket for years. Wherever I am in the world, I can grab a handful of Maine. Stay clear of the east side of the island because it is a bird nesting area.

By early afternoon it will be time to gather up the crew and return to the boat for lunch and a discussion of what to do with the remaining days of the trip.

Day 11: Six miles north of Brimstone, halfway up the eastern shore of Vinalhaven, is Seal Bay, a nifty piece of water with anchorages, coves and islands. The entrance is between aptly named Bluff Head and Hen Island. The channel is narrow and the current swift, but inside there are five or six individual and secluded anchorages. You’ll be surrounded by a granite and spruce wilderness. The only trail access is through Huber Preserve, south of Burnt Island. With a kayak or the dinghy, you can explore the coves and islands, and watch wildlife, birds, dolphins, foxes, and perhaps see a deer. Next to Seal Bay is Winter Harbor, another narrow cove cut deep into the island. There are three or four spots to anchor, but mind the current and swing room.

Days 12 and 13: It’s time to get back into civilization, and cellphone service. Let’s head to Camden. This is a morning trip from Seal Bay. Head up through the Fox Island Thoroughfare, put the Sugar Loaves to port this time, and turn right at the Fiddler, a granite stone monument at the southern end of a ledge off Stand-In-Point. From there, it’s an 8-mile dash across West Bay to Camden. Watch out for the Graves, a ledge above high tide, marked by a light, a mile and a half southeast from Camden.

Put Curtis Island Lighthouse to port as you enter Camden’s outer harbor. There’s room to anchor inside to the right, east of the mooring field, west of the ledges. The Yacht Club, Wayfarer Marine and the town have rental moorings. Call ahead. The inner-harbor floats are filled with local craft, but Wayfarer and the town docks might have space to come alongside. Wayfarer has a fuel dock and pump-out station. The town has a pump-out boat that will come to you in the outer harbor. Call ahead.

Ashore, Camden is as charming a town as you could imagine. It was the film set for the 1950s movie Peyton Place. There are shops, a library, provisioning, laundry, and on Wednesdays and Saturdays, there’s an open-air farmers market. There are hardware stores, T-shirt shops, and art and home-furnishing galleries. Camden has also become Maine’s foodie town, with more a dozen restaurants, featuring Italian, Asian and French cuisine, and good-old New England seafood. There’s waterfront dining, and Harbor Dogs—a fish-taco truck—is right there on the public landing.

There’s a large, freshwater lake nearby and half a dozen hiking trails that wander through the Camden Hills. A half-hour climb to the top of Mount Battie, which oversees Camden, provides stunning vistas of Penobscot Bay. You can see the islands you just explored, with views all the way to Blue Hill, Cadillac Mountain and Isle au Haut. The trail begins just a 10-minute walk from the dinghy docks.

In non-COVID times, there are concerts and plays, as well as performances on the library lawn and at the Opera House. Wandering the streets or hiking over the hill to Rockport will get you back in shape from two weeks of cruising. It’s so nice there, you could move in. I did.

Day 14: Last day—it’s back to Rockland, 7 miles south of Camden. The crew can pack up, unload and head back to civilization. The boat can get parked on a mooring until the next adventure, or take you south. From there, it’s roughly 36 hours to Newport, Rhode Island. Or you can haul the boat for the winter, with plans to sail farther east next summer.

You can also think about future trips.

Northern Penobscot Bay needs a visit, including Warren Island, a state park next to Islesboro Island with hiking trails. Then into East Bay to visit Castine Harbor, Smith Cove and a dinghy trip up the Bagaduce. There are small coves and anchorages such as Bucks Harbor, along Eggemoggin Reach. Swans Island is next, then up into Blue Hill Bay, over to Mount Desert Island and Somes Sound. That’s another two-week jaunt before returning west, back through the Deer Isle Thoroughfare, with stops in Stonington and the islands of Merchants Row. Then a day’s sail back to Rockland.

The opportunities are endless. This could become a habit.

The Challenges of Cruising Maine

here are a few navigational challenges I should mention, such as fog, 10-foot tides, 4-knot currents, anchoring among rocks and ledges, and lobster buoys and trap lines. I didn’t say cruising the coast of Maine was going to easy, but it can be an exciting challenge for any cruising sailor. I can think if no better place to test your skills while exploring one of the world’s great archipelagos.

Fog: There are three degrees of fog, I’m told. With “normal” fog, you can see a quarter-mile ahead. “Thick” fog is when you can see only a few boat lengths ahead. With “dungeons” of fog, it’s so thick, you can’t see the bow of your own boat. In the old days, Mainers practiced potato navigation: a kid on the bow with a bag of spuds tossing them ahead. A splash? Keep going. A thud? Tacking!

Today, AIS, radar, GPS, chart plotters and VHF have reduced the anxiety, but many lobster boats fail to use AIS, radar doesn’t see trap buoys and lines, and the currents haven’t changed. Someone on deck needs to keep visual watch while you are below glued to the radar screen. The sounder doesn’t help much in fog. Your keel could be in 30 feet of water with the bowsprit tangled up in the spruce trees ashore. The most valuable piece of equipment to have on board in fog is the anchor. Fog will burn off by late morning—if it’s going to. In June and early July, fog is more common, less so later in the summer. September is the best month in Maine.

Tides and current: Tides in Maine run 8 to 10 feet. That’s a lot of water to push up into the bays and drain back out, twice each day, at six- and 12-hour intervals. The tidal current running in and out of bays and coves can reach 4 knots. An hour’s run across the bay can set you off a mile on arrival, unless you compensate. With all those ledges and rocks lurking about, even a few feet off course can put you aground.

Anchoring means deploying sufficient scope to cope with the tidal range. Then there’s the set of the current: When the tidal current switches direction, where will your boat sit? Best to have a few anchors and extra line aboard to deploy in a Bahamian moor, to anchor astern or to run a stern line ashore.

Lobster buoys and trap lines: Lobster buoys are as much a hazard as fog and currents. Maine is prime lobster-fishing territory, with buoys so thick in places, you could walk to shore on them. The colorful buoys are not the problem—it’s the line that floats just below the surface from the buoy to the toggle. The toggle is a small float that keeps the trap line off the bottom, but when the tide is low, the toggle might reach the surface, and the 20 feet of line to the colorful buoy floats just below the surface.

Steer around the top of a buoy, not the bottom end where the line exits the base of the buoy. Do not go between the buoy and the toggle; you’re liable to find that you’ve snagged the line and fouled the prop. This might require a dive overboard into frigid water to cut the line free. And in most places, the sea rarely gets above 60 degrees, even in the middle of the summer. Lobster boats have a wire cage around the prop to keep out their trap lines. You can have a line cutter bolted to your prop shaft to cut the line, but then the fisherman has lost his trap. Radar doesn’t see the buoys, and you can’t see them at night. Keep a constant watch when navigating in Maine, and steer clear of buoys and trap lines. Even sailboats with their prop locked can snag a line on the blades or the rudder. Divers can be hired in many harbors to free a fouled prop. Still, lobster buoys are helpful in seeing which way the current flows and at what speed.

Prevailing winds: A midsummer day in Maine is apt to be under a high-pressure system, resulting in sunny, fog-free days but little wind, especially in the mornings. As the land heats up, a southwest sea breeze is likely to fill in after lunch, and might get up to 20 knots by late afternoon, just before dying off before dark. Gales are infrequent in the summer, and when a low comes up the East Coast, it tends to pass by just offshore to the east, producing northeasterly winds. Most Maine bays and harbors are open to the southwest, providing a lee to those winds. Hurricanes are infrequent.

David H. Lyman is journalist, author, photographer and sailor. He sailed into Maine in the early 1970s and started a summer photography school, the Maine Photographic Workshops, which continues today as Maine Media Workshops ( mainemedia.edu ). He has been owned by four different sailboats, from an Alden 34-footer to a Bowman 57. He has sailed the entire East Coast, and made more than 24 offshore voyages between Maine and the Caribbean. His first memoir about his hitch as a Navy photojournalist with a Seabee outfit in Vietnam in 1967 was published in 2019. He lives and writes in Camden, Maine.

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Circling Maine's Penobscot Bay

Taking a boat "down east" can be a gauntlet of lobster pots, fog, and double-digit tidal swings that keep you on your toes. four buddies dealt with it an on a treasured summer charter..

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For many first-time boaters in Maine, the big surprise is not the extreme tides, fog, or granite ledges sometimes right below the surface — it's the lobster traps! Lobstermen set about 3 million traps in Maine each year, and in some places the water seems paved with their colorful floats, just waiting to snag your prop.

Once you gain some local knowledge about lobster traps, their submerged lines, and some experience around them — that happens quickly! — it's just another reason why boating in Maine is so unique. Penobscot Bay, the heart of Maine cruising, offers some of the most spectacular boating to be found on the planet: countless inviting islands and protected harbors to explore, pine-covered mountains, pink rocky coast, quaint fishing villages, high-end tourist towns, and generally moderate prevailing southwesterly winds.

Setting off Down East

Our August Penobscot cruise consisted of a group of sailors who bareboat charter boats someplace different every year. For this seven-day trip, we filled several boats from two charter companies. Our own four-man crew was on Redwings , a comfortable 46-foot center-cockpit sloop.

There's more than enough magnificent coast here to spend a lifetime exploring, though we got a good taste for why this place is so special in a week. But "special" doesn't mean "easy." Navigating the beach bars in the Caribbean is a world away from the challenges that awaited us along the coast of Maine.

"People often believe that if they've sailed in other places that they're a capable sailor in Maine," says Larrain Slaymaker, owner of NorthPoint Charters in Rockport, who's been in the business for almost 35 years. "That's not always the case." This may be changing for the better though. Max Johanson, service manager of Johanson Boatworks in Rockland, the largest charter boat brokerage in the region, says he's seen more boaters prepare by getting certified through ASA, USSailing, Offshore Sailing, or other formal boat and navigational training. "People are paying more attention to the navigation, and we push that pretty hard," he smiles. "Up here, things go ‘bang' instead of 'squish' when you go aground."

Fog, rain, and strong wind can set in anytime, too, but there are countless gorgeous protected hideaway anchorages to tuck in when it does. Luckily, we savored some of Maine's pristine, calm and warm days — clear air, visibility unlimited, as aviators like to say. The cruising season is short up here, too (typically late June through early September), so we prepped for all weather.

Our weeklong circuit hit many of the most beautiful and interesting highlights in Penobscot Bay.

Fellow cruiser Scott Taylor retrieves a line fouling the prop on Elusive, a C&C 40 in Seal Cove off Winter Harbor. (Photo: Peter Willsea)

Rockland, where most of our group set out, is the largest harbor and town in the bay and home to Johanson Boatworks, which supplied our boat. It's a busy harbor crammed with power- and sailboats of all stripes, workboats, and windjammers. There are several marinas, including Rockland Landings Marina and Journey's End Marina. North End Shipyard is home to some of the harbor's classic windjammers, a sight to behold.

Rockland deserves extra time to explore, with such attractions as the beautifully restored Rockland Breakwater Light, the world-famous Farnsworth Art Museum, the Apprenticeshop wooden boatbuilding school, and the Sail Power and Steam Museum. Among the big summer events here are the Maine Lobster Festival (July), and the Maine Homes, Boats and Harbors Show (August) — with its beloved World Championship Boatyard Dog Trials.

Redwings at Outer Scott Island. (Photo: David Crichton)

Camden, just north, is one of the prettiest summer tourist colonies in coastal Maine. It's also a major yachting center, with a busy, well-protected harbor, guarded by Curtis Island Light at the southern entrance. Call ahead if you want a mooring in Camden (Wayfarer Marine manages most of them), or expect to anchor out by the harbor entrance.

This is where our four-man crew picked up our charter boat at the small municipal floating dock, across the harbor from the Camden Yacht Club. With no wind our first day, we motored northeast past Islesboro Island, arriving before sunset at remote Bucks Harbor, a popular and cozy hurricane hole at the northern end of Eggemoggin Reach. But instead of looking for a mooring there, we headed over to the next inlet west, anchoring halfway up fjord-like (and empty) Orcutt Harbor, and were soon sitting down to a dinner of fresh pan-seared Maine scallops and crisp wine, savoring the nearby forest scents and quiet solitude.

Down East Cruising Tips

• Watch those lobstah pawts. Know your boat underwater. Do you have a spade rudder and fully exposed prop, both vulnerable to a snag? While some traps are "singles" (tied to their own line), many are attached to a long line (the potwarp) that connects multiple "pots" on the bottom. Snagging a potwarp on the prop and having it wrap and fuse around the shaft will shut down the engine and anchor your boat to a chain of lobster pots. The 50-something-degree water can be dangerous. Don a heavy wetsuit or call ashore for a diver if necessary.
• Fog. It sets in any time but most likely occurs in July and August. Patchy fog is beautiful. But thick, blanketing fog is disorienting and creates the risk of running down (or being run down by) other boats. Charter companies recommend that cruisers plan to include a lay day to wait out the fog.
• Tides, ledges, & moorings. Tidal range up here can run up to 18 feet and tidal currents can be strong, so pay close attention to chart depths, tide tables, and know where you are in the cycle. Submerged ledges are well charted. Study each route closely for shallow spots and keep a sharp lookout for locally disturbed or breaking water, indicating a ledge.
• Mooring and anchoring out. You need to know how to anchor and pick up, secure, and cast off from a mooring, as you're likely to tie to one at some point. They fill fast in busy harbors, so reserve dock space or a mooring in advance, or show up early to find a decent anchoring spot.

For more Down East cruising tips and how to choose the best charter see " More Maine 'Down East' Cruising Tips ".

The Road To Mount Desert Island

We woke to thick fog, hiding even the nearby shore. After devouring omelets and sausages, we fired up the radar and GPS and very slowly motored out of the harbor with a lookout on the bow for boats, pots, and markers. When the fog lifted, we had a gorgeous view of Eggemoggin Reach, one of the prettiest stretches of water in Penobscot Bay, separating Little Deer and Deer islands from the mainland. On the eastern end of the Reach is the small town of Brooklin, picturesque home to Wooden Boat magazine and its Wooden Boat School, where boaters can visit, along with the revered Brooklin Boat Yard, a custom builder of gorgeous power- and sailboats of classic lines.

Leaving Eggemoggin Reach, we sailed east and crossed Jericho Bay, heading our way through the narrows of Casco Passage and entering Blue Hill Bay, with Mount Desert Island ahead. Just past Bass Harbor Bar at the southern tip are the shallows of Western Way, an easy passage between Mount Desert and the Cranberry Isles for all but the deepest-draft cruisers, and a convenient shortcut to two of Maine's top cruising destinations.

A lobster boat in the fog in Pulpit Harbor. (Photo: Stephen Blakely)

Northeast Harbor, due north, was once known as "Philadelphia on the rocks" for all the blue bloods who summered there. The small town is a short walk up the hill from the marina and offers "Old Maine" village charm. Just west of here is the narrow, deep fjord of Somes Sound.

Nearby Southwest Harbor to the west, the bigger and more protected of the two, is headquarters to such semi-custom boatbuilders as Hinckley Yachts, Morris Yachts, and Ellis Boat Company. Popular sites here include Beal's Lobster Pier, and Dysart's Great Harbor Marina, a sprawling modern facility that's a big draw for cruising clubs and huge private boats sporting uniformed crews and tax-haven flags of convenience. A short walk from the marina is the small village of Southwest Harbor with great stores, galleries, and restaurants.

Camp Island anchorage near Stonington. (Photo: James Evangelisti)

On the east side of Mount Desert is Bar Harbor, the island's tourist Mecca often overwhelmed by crowds from cruise ships and land yachts. This is the hub for the free Island Explorer shuttle bus that circles the island, making all of Acadia National Park ("the crown jewel of the North Atlantic coast") easily accessible to cruisers from any major harbor on the island. Do. Not. Miss. Acadia.

Penobscot Bay Resources

• Maptech Penobscot Bay to Mount Desert Island, Ed. 2
• NOAA Booklet Chart 13305, Penobscot Bay

Charter Firms

Prices for a weeklong charter depend on the boat but generally range from $5,200 a week for a Bristol 43 and Beneteau 445 to $2,000 for a Dufour 35.

• Johanson Boat Works (JBW) , Rockland
• NorthPoint Yacht Charters , Rockport
• Bucks Harbor Marina , South Brooksville
• Cruising Guide: "A Cruising Guide to the Maine Coast," Hank and Jan Taft, Curtis Rindlaub (Sixth Ed.), $50 paperback. The bible for these waters, known simply as "the Taft."
• Lobster Pot and Gear Configurations in the Gulf of Maine
• Maine Windjammer Association

NOAA Tides & Currents

• Tides & Currents Predictions

The Maine Islands Trail

America's first recreational water trail for small boaters, running 375 miles from the New Hampshire border to Canada. It connects more than 200 wild islands and mainland sites open for day use or overnight camping. mita.org

Closing The Circle

Our third day out, we got an early start sailing south around Swans and Marshall islands, then west into Merchant Row. This is a beautiful maze of dozens of small, remote, and mostly uninhabited islands between Deer Isle and Isle au Haut, with many excellent anchorages surrounded by pink-hued granite fringed in lush evergreens. We anchored that evening in the calm shelter between Camp and Devil islands, just east of Stonington at the southern end of Deer Isle.

If Stonington is a frontier town, as it's been described, then lobstermen are its rough-and-ready cowboys. This is home to more than 300 lobster boats, and the annual Stonington Lobster Boat Race in late July is a big deal.

A lobster boat’s prop cage. (Photo: Stephen Blakely)

Early the next morning we cruised past Stonington and dropped south. After several days of dodging lobster pots, the crew of Redwings decided it was time for revenge, so we sailed to Isle au Haut for what turned out to be the sweetest — and most expensive! — lobster rolls of our voyage, consumed at an outdoor picnic table, yards away from the lobster boats that had brought in our lunch just hours earlier. About half of this wonderfully isolated island is part of Acadia National Park, which offers magnificent hiking, a wealth of wildlife, and striking biodiversity. The still-active Robinson Point Lighthouse is now part of a high-end B&B, The Keeper's House. The small harbor here can be too shallow to transit at low tide, so time your visit.

After lunch we headed back out and quickly ran into a chilly fog bank, navigating by chartplotter and sound (the radar having decided to take a vacation), keeping all ears out for bell buoys or other boats, and periodically ringing our ship's bell. With a gale forecast to arrive that night, we sailed for Pulpit Harbor on the west side of North Haven Island, one of the best hurricane holes in Penobscot Bay. There are no public facilities in the harbor, but provisions are available a mile walk away at North Haven Groceries.

The Stonington Opera House overlooks the busy working waterfront. (Photo: Stephen Blakely)

North Haven and its larger sibling to the south, Vinalhaven, are part of the Fox Island archipelago and are separated by Fox Island Thorofare, one of the most dramatically beautiful stretches of water in Penobscot Bay. We motored westward past Goose Rocks Light into the Thorofare of rocky islets and boulder configurations, beautiful homes peeking out, and classic windjammers sailing through.

The author on the right as Redwings sails to Isle au Haut. (Photo: David Bird) 

This was our last night at anchor, in the picturesque harbor off Dix Island at the northern end of Muscle Ridge Channel, in Penobscot's southwestern corner. Dix and neighboring Birch Island are privately owned, but boaters are welcome to hike the trails as long as they respect private space and not make campfires.

Our sixth day involved a short sail southwest to the mainland village of Tenants Harbor, an excellent harbor of refuge. Tenants Harbor Lighthouse on the south point appears in paintings by the late Andrew Wyeth and his son Jamie Wyeth — not surprisingly, since the family has owned the lighthouse since 1978.

Early the next morning we sailed back up to Rockland, drifting in light air and a fair tide through Muscle Ridge Channel. The highlight was passing Owls Head Light, one of the most charming — and said to be the most haunted — of all the lighthouses in Maine. It was a short leg back around Rockland Light and into the harbor, where we closed our circle.

We'd stretched ourselves, dealt with 18-foot tides, shrouds of unexpected fog, and sometimes massive obstacle courses of lobster pots. But we'd done it with more laughter than hair-raising drama, and we ate like kings. It was one of the best boating trips of our lives.

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• A Day on the Maine Island Trail
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Stephen Blakely

Contributor, BoatUS Magazine

Stephen Blakely cruised Chesapeake Bay for many years on Bearboat, an Island Packet 26, and now trailers a 13-foot Mellonseed skiff, Watermelon, to explore his new home waters of Cape Cod.

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EVENING STAR YACHT CHARTERS

Maine Bareboat Yacht Charters

Sail the Coast of Maine on a Beautiful Classic Sailboat

Looking to charter a bareboat yacht on the coast of Maine?   Evening Star   is a 45' traditional sailboat available for bareboat charter from Belfast Harbor in the heart of Penobscot Bay!   The yacht Evening Star is equipped with Hood Stowaway roller furling masts and has two double staterooms, each with its own head and shower.  

Now Taking Reservations for 2024      Available Bareboat or with Captain

• Orland Tourism
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Penobscot Bay Yacht Exchange Ticket Price, Hours, Address and Reviews

• North America
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• Things To Do In Orland

Penobscot Bay Yacht Exchange

• Address: 47 Wardwell Rd, 04472, Orland, United States
• Tags: Sports And Recreation, Water Sports, Boating

Penobscot Bay Yacht Exchange Reviews & Ratings

Attractions Nearby

• Mount Hope Cemetery
• Paul Bunyan Statue
• Cole Land Transportation Museum
• Blackbeard's Park
• Darling's Waterfront Pavillion
• Bangor Mall
• The Rock And Art Shop

Pen Bay Custom Charters

Departing from Castine, ME the M/V Retriever & crew of experienced professional mariners are ready to take up to 6 passengers by appointment anywhere in the Penobscot Bay area & beyond.  Fast, efficient & comfortable, this 30' picnic boat is the perfect match for a great day on the water.  From Castine harbor tours to full day excursions on Penobscot Bay or a variety of marine transportation tasks; we are ready for any adventure with a flexible schedule based on your needs Check out the gallery below!

• 305-923-3740
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Our Maine Yacht Charters

5-star service, tailor-made itineraries.

Leave the world behind as you step aboard the Indigo Luxe Yacht. Enjoy the combination of elegance with life’s simple pleasures as we gently cruise across the turquoise oceans surrounded by incredible views. Our unrivaled customer service allows our guests to tailor-make their itineraries and customize anything down to the last detail, so sit back and relax on the spacious deck with a cocktail in hand while our professional crew takes care of everything.

Indigo is available for charter for up to 6 people with or without catering. Our onboard menu is provided by the chef of Indigo catering kitchen, who are able to cater to your every need. Please note that custom charters are available upon request, so send all inquiries to one of our friendly team members and we will endeavor to reply in a timely manner.

Our Charters

Lighthouse Tour (3 Hours)

Cruise along the midcoast shoreline discovering 3 of the area’s most beautiful and historic Lighthouses: Curtis, Rockport and Rockland. Spot local seals, porpoise and enjoy the beautiful breezes the Penobscot Bay has to offer. Travel fee may be added based on pickup location. Add additional time at $500 for each additional hour, plus tax and gratuity.

$1,295 + 20% gratuity. *Fuel surcharge may apply based on your requested activities.

1/2 Day Cruise & Adventure (4 hours)

Plan a morning or afternoon of cruising across Penobscot Bay to one of the many islands only accessible by boat.  Hike Warren Island National Park, visit Goose Cove on Deer Isle, or visit Seal Island.  Bring a picnic lunch or have our crew arrange lunch aboard.  This trip is a wonderful way to see Midcoast Maine from a different point of view. Travel fee may be added based on pickup location. Add additional time at $500 for each additional hour, plus tax and gratuity.

$1,595 + 20% gratuity. *Fuel surcharge may apply based on your requested activities.

Full Day Excursion (5 – 6 Hours)

Cruise to a distant magical island like Monhegan or cruise the coastline North to a quaint port such as Belfast. Visit Vinalhaven, North Haven, Stonington or any one of the many islands accessible in Penobscot Bay. Our professional team will put together the perfect itinerary for your group from start to finish and create a custom charter personalized to your every desire. Travel fee may be added based on pickup location. Add additional time at $500 for each additional hour, plus tax and gratuity.

$2,595 + 20% gratuity. *Fuel surcharge may apply based on your requested activities.

Add kayaks or catering for additional fees. Please enquire with our sales team when booking.

Custom Charters

Sail to Vinalhaven, North Haven, Stonington or any one of the many islands accessible in Penobscot Bay. Our professional team will guide you from start to finish and create a custom charter personalized to your every desire. We host micro weddings, cocktail hours, photoshoots, waterfront real estate showings, company outings, and the list goes on. Charters are available to be be booked for up to 3 nights & 4 days. We will ensure your every need is met and your expectations are exceeded—the possibilities are endless.

Pricing starts at $3,500 + 20% Gratuity per night. *Fuel surcharge may apply based on your requested activities.

Maine Pickup Locations

Indigo is docked in the pristine Penobscot Bay in Camden, Maine and charters leave from various pickup locations.

We can pick up at your approved location in Penobscot Bay, available upon request. Please inquire about our approved public docks for pick up.